9 Best Canoes & Kayaks In Chicago

Bike Tours, Canoes & Kayaks, Chicago, Cycling Tours, Food, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago: Classic Food Walking Tour with Bike or Kayak Rental

/ June 4, 2026

1.Chicago: Classic Food Walking Tour with Bike or Kayak Rental

3-hour guided Chicago classic food walk with deep-dish pizza, hot dogs, Italian beef, brownies, plus free 2-hour bike or kayak rental.

Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach

/ June 14, 2026

2.Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Rent a single or tandem kayak at Ohio Street Beach and paddle Lake Michigan near Navy Pier for 1 to 2 hours with optional beach time.

★ 5.0

“La verdad llego muy tarde solo nos dio el cayac y nos dejó ala deriva aun no nos dijo más nada la verdad fue pésimo y no lo volvería a agarrar”

22 reviews1 to 2 hours (approx.)From $39.99by Bobby's Bike, Hike & Food Tours - Chicago

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2-Hour Experiences, Canoes & Kayaks, Chicago, Tour Reviews

Chicago: 2-Hour Downtown Kayak Rental

/ June 15, 2026

3.Chicago: 2-Hour Downtown Kayak Rental

Paddle Chicago River downtown on a 2-hour kayak tour with a safety-first lesson, single or tandem options, and skyline views.

★ 4.5

“It was so much fun”

19 reviews2 hoursFrom $62by Wateriders Kayak Tours & Rentals

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Canoes & Kayaks, Chicago, Tour Reviews, Tours

Chicago: Moonlight Paddle Tour on the Chicago River

/ June 20, 2026

4.Chicago: Moonlight Paddle Tour on the Chicago River

Night kayak on the Chicago River for 1.5 hours, with moonlit skyline views like Willis Tower and Marina City.

★ 4.2

“It was ok. The tour needs to be more organized. People were all over the place didn’t know where we was going what we was doing besides making sure not getting hit by a big boat.”

9 reviewsFrom $58by Wateriders Kayak Tours & Rentals

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Canoes & Kayaks, Chicago, Evening Experiences, Tour Reviews, Tours

Chicago: Sunset Kayak Tour on the Chicago River

/ June 26, 2026

5.Chicago: Sunset Kayak Tour on the Chicago River

Paddle the Chicago River at golden hour for skyline views, Willis Tower and the Civic Opera Building, plus a calm 90-minute guide-led tour.

★ 4.2

“Eindrückliche Kanu-Tour inmitten von Chicago beim Einnachten… Leider etwas chaotisch organisiert mit Kanus, die viele Reparaturen nötig hätten. Von den Guides keine Hinweise/Erklärungen zur Tour 😳”

5 reviews1.5 hoursFrom $57by Wateriders Kayak Tours & Rentals

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Bike Tours, Canoes & Kayaks, Chicago, Cycling Tours, Tour Reviews, Tours, Walking Tours

Chicago: Best of Attractions Walking Tour +Bike/Kayak Rental

/ June 27, 2026

6.Chicago: Best of Attractions Walking Tour +Bike/Kayak Rental

A 2-hour Chicago walking tour of top landmarks plus a free 2-hour bike or kayak rental within 3 days. Great value for first-timers.

★ 5.0

“It was fantastic learning about the history of the area”

5 reviews2 hoursFrom $44by Bobby's Bike, Hike & Food Tours - Chicago

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Bike Tours, Canoes & Kayaks, Chicago, Cycling Tours, Sightseeing & City Tours, Tour Reviews, Tours, Walking Tours

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

/ June 26, 2026

7.Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

Chicago highlights walk plus free 2-hour bike or kayak rental, covering Millennium Park, the Riverwalk, The Bean, and more.

★ 5.0

“Food was great, learning the history from our tour guide Mickey was fun. Our kids love history and they really enjoyed it!”

5 reviews2 hours (approx.)From $44.99by Bobby's Bike, Hike & Food Tours - Chicago

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Canoes & Kayaks, Chicago, Guided, Historical Tours, Tour Reviews, Tours

Chicago: History and Architecture Guided Kayak Tour

/ July 2, 2026

8.Chicago: History and Architecture Guided Kayak Tour

Guided kayak on the Chicago River through downtown history, drawbridges, reverse flow, and skyline views. Small group, 2 hours.

★ 5.0

3 reviews2 hoursFrom $64by Wateriders Kayak Tours & Rentals

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Bike Tours, Canoes & Kayaks, Chicago, Cycling Tours, Food, Food & Drink, Sightseeing & City Tours, Tour Reviews, Tours

Chicago in a Day: Food & Walk Tour+Free Bike or Kayak Rental

/ July 3, 2026

9.Chicago in a Day: Food & Walk Tour+Free Bike or Kayak Rental

Chicago in a Day food-and-walk tour with 5 tastings and free 2-hour bike or kayak rental. Downtown landmarks plus iconic eats.

★ 4.2

“My booking was moved to a different tour called “Chicago Favourites” as the one I originally booked was undersubscribed. It wasn’t really worth the money -the additional $20 for the “3 craft beer pairing” and the recommended $10-15 tip taking it over $100. For that price we got a slice of pizza, a small hot…”

3 reviews5 hoursFrom $99by Bobby's Bike, Hike & Food Tours - Chicago

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Canoes & Kayaks